Their First Time
by J.W.H. 10
Summary: Tails and Zooey lose their virginities. (Requested)


**A/N: This story is a request.**

It had been going on for ten minutes.

Both foxes were sitting on the couch, wrapped in each other's groping arms as they made out with passion. Lips smashed together, tongues twisting.

The vixen slowly pulled away. "Um, Tails?"

"Yeah, Zooey?" The fox answered.

"Do you... think we're ready to go there?" Zooey timidly asked.

"What are you talking about?"

"I'm... talking about sex." Zooey blurted out with a blush at her cheeks.

"Oh..." That brought a taint of red to Tails' cheeks as well. "Well... why do you ask?"

Zooey looked away as she answered. "It's because... well, lately, I've been... having these urges whenever we make out. Like we should just go ahead with it. But I always feel scared. And when you leave, I become so horny, I end up fingering myself."

"OK... but do you feel ready?" Tails asked.

Zooey looked at him curiously. "Why do you ask?"

Now it was Tails' turn to look away. "Because... I feel the same way."

Zooey gasped. "Really? Then why weren't you saying anything?"

Tails looked at the floor as he answered. "I was afraid to bring out the subject lest you saw me as a pervert who was only dating you for your pussy."

Now, Zooey burst out laughing. "Tails, I know you. You would never do that to me." She took his hand in her own. "And the fact that you were also scared kind of makes me feel better. And less scared."

Tails gently cupped the vixen's chin. "So... shall we continue?"

Zooey answered by smashing their lips together and wrapping her arms around the fox's neck. She then broke the kiss and looked at her boyfriend dead in the eyes. "Tails... I think I'm ready."

"You think?" Tails raised an eyebrow.

The vixen rolled her eyes and sat on Tails' lap. "Yes, Tails. I'm ready for you to pop my cherry." She smothered him with another kiss before he could speak. To send the message clearly, she grinded herself onto his crotch.

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Tails grabbed Zooey's ass and lifted her up. She instinctively wrapped her legs around his waist for support and could feel his growing arousal between her legs. The sensation was enough to set her juices flowing. He carried her up the stairs to his room and set her down on the bed. He momentarily broke the contact between their lips.

"Just to be sure you're not having second thoughts..."

Zooey's response was a growl and an impatient tug on his shirt. "I'm sure, Tails. I really need this." Just to prove to him how eager she was, she flipped them over and wound up on top, straddling her boyfriend.

Tails then grabbed her shirt and pulled it over her head. Her slightly large breasts jiggled in the confines of her bra. He had long since fantasized about seeing them in all their glory; without hesitation, he reached behind her back and unfastened the bra. The garment fell off, unveiling those wonderful globes of flesh to his hungry stare.

Zooey giggled at the effect her bust had on the two tailed vulpine. "You boys are all the same." She giggled as she felt his dick throb underneath her. She slid down his legs to undo his belt and then brought his trousers and boxers down and off in one swift motion.

She gasped when she gazed at his fully erect dick, now free from the confines of his boxers. "Wow... it's so big." With a trembling hand, she wrapped her fingers around its girth and slowly stroked it.

Tails' reaction was instantaneous. He arched his back and let out a sharp moan. The vixen took it as a good sign and repeated her actions, this time speeding up her strokes. Tails emitted another sharp moan and pre-cum oozed from the tip of his dick.

Zooey used her thumb to spread the sticky fluid all over the bulbous tip. "Does that feel good, baby?"

"Oh, you know it" Tails moaned.

"Good, coz I'm just getting started." She winked seductively and then once again turned her attention to his manhood. "You're gonna like this, Tails."

Zooey stuck out her tongue and lapped at the dick's head. More pre-cum oozed out and slowly dribbled down the shaft. She stole a glance at her boyfriend's face. Tails had his eyes closed and was panting hard, his chest heaving up and down. The vixen giggled at the effect her foreplay was having on him. "I haven't even started giving you head yet and you're already like this?"

Tails opened his eyes and grinned. "H- hey... y- you know it's my first time."

"Then I hope you can hold in longer." Zooey smirked.

Before Tails could ask what she meant, Zooey took his pre-cum covered dick into her mouth. The fox instantly arched his back upwards and released a loud moan. "Oh, fuck!"

Although Tails could not see it, Zooey smiled at his reaction. She started to bob her head up and down his length, licking the pre-cum off. It had a salty-sweet taste to it. She popped her mouth off momentarily to comment, "Mm, tasty." And resumed sucking.

Tails put his hand on the back of her head. She got the hint and sped up her ministrations. Pleasure enveloped the two tailed fox's system as he felt himself getting closer and closer to orgasm. When it came, he threw his head back and moaned with pure bliss.

Zooey felt Tails' dick pulse and a blast of sticky cum shot into her mouth, followed by another blast. Her cheeks swelled up with the amount of sperm filling her mouth, she thought it was going to leak out. Fortunately, Tails moaned one last time as he released his final cum blast. The vixen smirked at her boyfriend's spent look. She lightly slapped his cheek to get his attention. When he looked at her, she opened her mouth to show him the white fluid before closing her mouth and swallowing it.

"Yummy."

Tails sighed with content. "That was erotic." Then he suddenly grabbed her by the shoulders and flipped them over, pinning her under him. "I think I should return the favour."

He slid down her body and came to her skirt. Lifting it up, he exposed her panties, which were thoroughly soaked in her juices.

"Wow, someone's overexcited." He quipped.

In response, Zooey grabbed the back of his head. "Shut up and get down there."

Tails smirked before grabbing the soaked panties and sliding them down the horny vixen's legs. He gazed hungrily at her glistening pussy. "Wow, Zooey you're soaked." He stuck a finger out and ran it down the slit before pushing it inside.

Zooey moaned out loud and thrust her sex upwards. "Oh, my goodness!"

Tails smirked. "I haven't even begun doing anything."

"Stop teasing." Zooey bit back, thrusting her hips to get the fox to start.

He needed no second invitation as he started to pump his finger in and out of her pussy. More and more juices started to leak out of her hole as the vixen thrashed and grabbed a fistful of the sheets. Her moans slowly increased in volume as she was pleasured by her boyfriend's finger.

Tails added another finger and Zooey's moaning and thrashing doubled.

"Yes, that's it, Tails... I think I'm getting close... oh."

Tails completely withdrew his fingers, which were now glistening and dripping with pussy juice.

"Hey, what gives-" she did not get far in her complaint when she saw her boyfriend move his head down in between her legs.

"I wanna taste you too." Tails said before he dove in. His tongue easily parted the sensitive flesh and made its way into her hot core.

Zooey almost shot out of the bed as her rapidly diminishing pleasure returned with a vengeance. She clutched the sheets so hard, her claws dug holes in the cotton.

Tails continued to thrust his tongue in and out of her pussy before he decided to speed things along. His dick was erect again and was pulsing with a vengeance. Using his fingers, he parted the lips at the top of Zooey's pussy to expose her clit: the weakest spot on a female's pussy. He withdrew his tongue and concentrated on that sensitive nub.

Zooey's lust was pushed past its limit as she screamed so loud and clutched her boyfriend's head to keep him in place. She was so close, she could feel it coming, getting closer...

The entire room was filled with an ear splitting scream as the vixen had her very first orgasm caused by someone else. She bucked her hips off the bed as she shot a stream of juices straight at her boyfriend's mouth.

Although Tails was expecting a rush of fluid, he did not expect it to be that sudden or powerful. His mouth filled up in less than a second and before he could close to swallow, his muzzle was already wet and dripping. Fortunately, the gush of juices stopped. He lifted his head up from between her legs before climbing up to look at her face.

"You taste so sweet."

Zooey was panting like a marathon runner and a thin coating of sweat covered her golden fur. "That was- that was just amazing! Way better than when I do it myself.

Tails kissed his panting girlfriend and shoved his tongue into her mouth, giving her a taste of her own juices. She sucked on it until she could taste herself no longer and then broke the kiss to run her tongue all over his muzzle to get every last drop. She stopped when she felt something warm and hard poke at her thigh. Without hesitation, she spread her legs.

"I... guess this is it."

Tails nestled himself in between her legs. "You sure you want to do this?"

"Yes." Zooey whispered.

Tails positioned his dick at her pussy and slowly started to push it in. Zooey gasped as more and more of him entered her, stretching her insides to widths her fingers could never give her. Her inner walls were taking up a new shape, the shape of Tails' dick.

Tails also found himself experiencing a different level of pleasure. The inside of Zooey's pussy felt so warm, he thought his dick would melt. Her tight walls clamped around him as he stretched them for the very first time. His progress was slow but that was how he wanted it. She felt so deep, he thought he would not get to an ending.

But he eventually did, when he hit her hymen. Zooey gasped louder than before and Tails could sense a hint of pain behind it.

"It's OK, Zooey. Just look at me." Tails cooed.

The vixen wrapped her arms around Tails' neck. If she was going to go through that much pain, then it would be soothing at most if she held her boyfriend close. "Go ahead." Her voice was barely a whisper as she shut her eyes and braced herself.

Tails took a deep breath and pulled out a little before thrusting back all the way in. He almost went deaf at the sharp shriek of pain Zooey let out. She clutched at his neck so hard, he thought he felt a spine crack.

"You OK, baby?" Tails asked as he waited for his now deflowered girlfriend to open her eyes.

"I'm... fine, Tails. I'm just... waiting for the pain to subside." Zooey breathed. It took a while but the pain finally went away. She gyrated her hips a little to give him the sign to start.

This time, when Tails pulled back and thrust back in, there was no pain, only pleasure. Zooey moaned and allowed herself to relax as her boyfriend slowly made love to her. She looked up, into his blue eyes and saw the deep love he held for her. He had earned the right to pop her cherry with that love. She opened her mouth to say something but the only sound that escaped was a moan.

Tails smiled at her as he picked up the pace and started to build a rhythm. He felt he had stretched her pussy out far enough as he could now move more freely than before. Glancing down at Zooey's euphoric look only made him want to speed up more.

Zooey could only moan and squirm every time her boyfriend's dick penetrated her. He had started hitting her G-spot and she muttered the occasional "yes, right there." Every thrust brought her closer and closer to that very ultimate end. The vixen wrapped her arms around her lover's neck and her legs around his waist.

"Tails... I'm cumming! Unh!" With her last scream, she squeezed her arms and legs around her boyfriend as her pussy contracted around his dick and her juices leaked out.

Tails could feel the warm juices spray his dick. That and the rhythmic contractions of Zooey's pussy massaging his dick sent the fox over the edge as he thrust into her one last time before he erupted. A low growl issued from his throat as the first spurt of his seed shot into the vixen's pussy, followed by multiple other spurts. Tails grit his teeth at the insane amount of pleasure he felt. As his dick stopped twitching, he allowed himself to relax and pull out of her before rolling onto her side.

Both vulpines lay there, sweaty and panting as they slowly recovered from their sexual bliss.

Zooey spoke first. "Oh, my God, Tails. That was so amazing!"

Tails exhaled through his nose. "Yeah." He answered with a slightly dazed look on his face.

"It was... almost like you knew what to do. To get me to cum at your very first time? You know, few people can manage that."

"Guess I'm just that good." Tails smirked.

"Oh, really?" Zooey challenged as she sat up. She swung a leg over Tails and straddled him. "Think you can manage that again?"

"Why don't we find out?" Tails countered as he pulled her down and mashed their lips together. Their mouths opened and tongues wrestled. Tails' hands roamed all over Zooey's body, caressing her breasts, rubbing her thighs and squeezing her ass. In no time at all, he was hard again.

Zooey raised herself and grabbed Tails' dick to line it up. She rubbed it softly against her dripping pussy lips, getting the tip all lubed up with her juices before sinking it in. She gasped at the feeling of penetration as her insides were stretched once more.

Tails' hands moved to Zooey's hips and he started to rock her to get her to start moving. "Hey, Zooey' it's your turn to do the work." He said playfully.

The vixen was still recovering from her momentary mini-orgasm. "Shut up." She sighed. Then she slowly raised herself before sinking back onto Tails' dick. She slowly repeated the rhythm until the pleasure started to shoot through her. As she rode her boyfriend's dick, she opened her mouth and allowed the arousing moans to escape.

Despite Zooey doing most of the work, Tails' hands were far from idle. They were everywhere on the vixen's body. Her breasts were squeezed and rubbed; her nipples were pinched and stimulated. His touch was enough to send her into new heights of pleasure. She threw her head back as her moans became shorter and louder.

Tails smirked as his touch had the desired effect on his little minx of a girlfriend. As she continued to ride him, his hands moved from her breasts, down to her ass. He gave both cheeks a good squeeze and rubbed them up and down. Then he drew his hands back and gave Zooey's ass a good spank.

The spank drew a squeak out of the vixen. But instead of pain, she felt a pleasant tingle on her ass that seemed to add to the pleasure she already felt. She found herself craving for more.

"Do... do it again." She moaned.

Tails smirked as he slapped her ass again, drawing a louder and longer moan out of his girlfriend.

Zooey seemed to enjoy getting spanked as that seemed to reenergized her. She started to slam onto Tails' dick with an aggressiveness she never knew she possessed. The bed started to squeak with every thrust she made.

"YES, TAILS! KEEP SPANKING ME! YES, HARDER!"

Her screaming slightly unnerved Tails. Was Zooey's first night of sex going to turn her to the sick, demeaning practice of sadomasochism? Or was the pleasure becoming too much for her and making her drop whatever inhibitions she was still holding in? He hoped it was the latter.

"Wow, someone sure is frisky." He grunted as his dick was assaulted by another hard thrust.

Zooey did not respond. She propped herself up on her arms to raise herself slightly but only to change from a kneeling position to a squatting one. Then she slammed down on Tails' dick once more. The new position offered more power whenever she thrust down. The vixen's juices started to drip out of her pussy and onto her lover's dick, slowly trickling down onto his balls, which had now started to contract. Her own orgasm was on its way also as she threw her head back and screamed.

"I'M CUMMING!"

Her pussy clamped down on Tails' dick as a wave of raw pleasure overtook her. Her juices gushed out of her pussy, splashing Tails, abdomen, covering his crotch and staining the sheets.

Her final thrust pushed Tails over the edge as he let out a howl. A copious amount of sperm shot out of his dick and spurted into Zooey's womb, filling her up and leaving a warm, pleasant feeling.

With her energy well and truly spent, Zooey collapsed on top of her boyfriend, panting heavily, their sweat-slicked bodies rubbing one another.

"Told you... I could... manage it again." Tails panted. In spite of himself, he smirked in triumph.

Zooey lifted herself off her boyfriend's dick, their mixed juices leaking out and running down her thighs. She rolled to the other side of the bed, still panting for breath. "Actually, I was doing all the work there."

Tails scoffed. "And I still made you cum." Then he reached for his pants and dug into his pocket. He fished out his phone and switched on the camera. "C'mere. I wanna remember this."

Zooey moved in closer and snuggled up to her boyfriend. Tails adjusted the phone's angle so that they did not look undressed. Then they both kissed and the fox took the shot.

The two foxes looked at the picture and smiled. A perfect memoire to remind them of their first time.

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 **A/N: I'm gonna have to hold off on taking requests. I'm still taking care of my other stories and I'm not even close to finishing either one. BTW some of you may have read in my profile that I was to start a new story this month. Well, sad to say that story has been postponed to... well, my estimate is four years from now. That's because I cannot be writing three stories at once (I'm barely getting past two). So, to anyone who was expecting that story, sorry to disappoint.**

 **Anyways, read this one and enjoy it. Next up, Dark Tails.**

 **J.W.H. 10**


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